Title: Pittsfield Guest Houses from CA $249 | Expedia.ca [Pittsfield Travel Guide](https://expedia.ca/Pittsfield.dx184066)[Hotels in Pittsfield](https://expedia.ca/Pittsfield-Hotels.d184066.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.ca/Pittsfield-Vacation-Rentals.d184066.Travel-Guide-VacationRentals)[Flights to Pittsfield](https://expedia.ca/Cheap-Flights-To-Pittsfield.d184066.Travel-Guide-Flights)[Pittsfield Car Rentals](https://expedia.ca/Car-Rentals-In-Pittsfield.d184066.Car-Rental-Guide)[Pittsfield Vacation Packages](https://expedia.ca/Pittsfield.d184066.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-02-20&endDate=2026-02-22&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-03-06&endDate=2026-03-08&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Pittsfield guest houses ![Exterior detail](https://images.trvl-media.com/lodging/124000000/123370000/123364300/123364293/84d48d73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Single Room, 1 King Bed](https://images.trvl-media.com/lodging/124000000/123370000/123364300/123364293/b710ae09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123370000/123364300/123364293/75c9d62d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123370000/123364300/123364293/bc925baa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Killington Haus [](https://www.expedia.ca/Killington-Hotels-Killington-Haus.h123364293.Hotel-Information) Killington 8.8/10 Excellent (10 reviews) "Great location to ski resort and excellent Ramen restaurant on site " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim CA $248 CA $273 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Killington-Hotels-Killington-Haus.h123364293.Hotel-Information) ![Interior detail](https://images.trvl-media.com/lodging/9000000/8380000/8370400/8370321/3a9d5306.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/9000000/8380000/8370400/8370321/b9040b95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Private Bathroom (Efficiency Apartment)](https://images.trvl-media.com/lodging/9000000/8380000/8370400/8370321/a99ba878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/9000000/8380000/8370400/8370321/6c57eb6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Trailside Inn [](https://www.expedia.ca/Killington-Hotels-The-Trailside-Inn.h8370321.Hotel-Information) North Sherburne 9.0/10 Wonderful (144 reviews) "The owners were terrific! The establishment was very clean & breakfast was delicious especially the oatmeal!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen CA $226 CA $249 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Killington-Hotels-The-Trailside-Inn.h8370321.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/112000000/111750000/111740100/111740098/762a9442.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111750000/111740100/111740098/d1620b95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/112000000/111750000/111740100/111740098/ae0fc31e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/112000000/111750000/111740100/111740098/9e2f7084.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Slopeside Estate Guesthouse: Ski On/Off, Hot Tub, Views! [](https://www.expedia.ca/Killington-Hotels-The-Apartment-At-The-Slopeside-Estate-House-Ski-OnOff.h111740098.Hotel-Information) Killington 9.4/10 Exceptional (54 reviews) "Our group had a wonderful stay. The ski out location is great and worked well even for our beginning skiers. The amenities were as described and the views are amazing. The property owner was extremely responsive when a minor issue arose. We highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ann C. CA $512 CA $1,196 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Killington-Hotels-The-Apartment-At-The-Slopeside-Estate-House-Ski-OnOff.h111740098.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-22&endDate=2026-02-23®ionId=184066&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Guest-Houses.d184066-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Guest-Houses.d184066-aaGuestHouses.Travel-Guide-Accommodation) ## Top Pittsfield Hotel Reviews ![Best Western Inn & Suites Rutland-Killington](https://images.trvl-media.com/lodging/1000000/20000/16500/16411/9898f616_y.jpg) ### Best Western Inn & Suites Rutland-Killington 10/10 Excellent "Staff was very attentive and helpful, rooms very clean and comfortable with well organized setting, breakfast was pretty good and it is included with your stay." [](https://expedia.ca/Rutland-Hotels-Best-Western-Inn-Suites-Rutland-Killington.h16411.Hotel-Information) ![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946_y.jpg) ### On The River Inn 10/10 Excellent "Everything from the manager to the staff to the room and food. 5 stars" [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![North Star Lodge and Resort](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/0612ebf1_y.jpg) ### North Star Lodge and Resort 10/10 Excellent "Staff was helpful and room was clean" [](https://expedia.ca/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.Hotel-Information) ![Comfort Inn Rutland - Killington](https://images.trvl-media.com/lodging/1000000/10000/4700/4621/15d4fef0_y.jpg) ### Comfort Inn Rutland - Killington 10/10 Excellent "Everything was great! The staff were very nice and the free breakfast is legit!" [](https://expedia.ca/Rutland-Hotels-Comfort-Inn-Trolley-Square.h4621.Hotel-Information) ![Turn of River Lodge](https://images.trvl-media.com/lodging/19000000/18550000/18540700/18540657/e79916d3_y.jpg) ### Turn of River Lodge 10/10 Excellent "Yes " [](https://expedia.ca/Killington-Hotels-Turn-Of-River-Lodge.h18540657.Hotel-Information) ![Summit Lodge](https://images.trvl-media.com/lodging/2000000/1110000/1102600/1102506/5da3617c_y.jpg) ### Summit Lodge 10/10 Excellent "Reasonable clean nice place to stay" [](https://expedia.ca/Killington-Hotels-Summit-Lodge.h1102506.Hotel-Information) ![Hampton Inn Rutland](https://images.trvl-media.com/lodging/2000000/1530000/1523000/1522922/f4f05fc2_y.jpg) ### Hampton Inn Rutland 10/10 Excellent "This was a wonderful hotel! Very clean, lots of parking, close to shopping/restaurants, friendly staff and great amenities. I would highly recommend if you were staying in the Rutland area!" [](https://expedia.ca/Rutland-Hotels-Hampton-Inn-Rutland.h1522922.Hotel-Information) ![The Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "Woodstock is a magical place! We love staying at the Shire! They really make it feel like home! So cozy! The staff is very friendly and accommodating! We will always stay at the Shire!" [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![Mountain Sports Inn](https://images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/7b3b252e_y.jpg) ### Mountain Sports Inn 10/10 Excellent "Friendly staff and comfortable room " [](https://expedia.ca/Killington-Hotels-Mountain-Sports-Inn.h1339833.Hotel-Information) ## Find out more about Pittsfield ## Pittsfield Guest Houses information | Number of reviews | 122 | | ----------------- | -------------- | | Accommodation | 5 Guest Houses | | Lowest Price | CA $249 | | Highest Price | CA $1,196 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [4 Star Hotels in Killington ](https://www.expedia.ca/4Star-Killington-Hotels.s40-0-d10780.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Chittenden ](https://www.expedia.ca/Chittenden-Hotels-Cheap-Hotels.0-0-d184042-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Chittenden ](https://www.expedia.ca/Chittenden-Hotels-Luxury-Hotel.0-0-d184042-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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